- Microwave-promoted synthesis of polyhydroxydeoxybenzoins in ionic liquids
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A microwave-promoted synthesis of polyhydroxydeoxybenzoins and -phenylpropanones has been developed, using bis{(trifluoromethyl)sulfonyl}amine (HNTf2) or BF3·OEt2 in an ionic liquid solvent.
- Hakala, Ullastiina,W?h?l?, Kristiina
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- Microwave-Mediated Synthesis of Anticarcinogenic Isoflavones from Soybeans
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Soybean isoflavonoids, 7,4'-dihydroxyisoflavone (daidzein), 7-hydroxy-4'-methoxyisoflavone (formononetin), 5,7,4'-trihydroxyisoflavone (genistein), and 5,7-dihydroxy-4'-methoxyisoflavone (biochanin A), were synthesized in high yields by cyclization of their corresponding ketones in a conventional microwave oven. Keywords: Microwave synthesis; isoflavones; daidzein; genistein; formononetin; biochanin A
- Chang, Yu-Chen,Nair, Muraleedharan G.,Santell, Ross C.,Helferich, William G.
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- Identification of enterodiol as a masker for caffeine bitterness by using a pharmacophore model based on structural analogues of homoeriodictyol
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Starting from previous structure-activity relationship studies of taste modifiers based on homoeriodictyol, dihydrochalcones, deoxybenzoins, and trans-3-hydroxyflavones as obvious analogues were investigated for their masking effect against caffeine. The most active compounds of the newly investigated taste modifiers were phloretin, the related dihydrochalcones 3-methoxy-2′,4,4′-trihydroxydihydrochalcone and 2′,4- dihydroxy-3-methoxydihydrochalcone, and the deoxybenzoin 2-(4-hydroxy-3- methoxyphenyl)-1-(4-hydroxyphenyl)ethanone. Starting with the whole set of compounds showing activity >22%, a (Q)SAR pharmacophore model for maskers of caffeine bitterness was calculated to explain the structural requirements. After docking of the pharmacophore into a structural model of the broadly tuned bitter receptor hTAS2R10 and docking of enterolactone and enterodiol as only very weakly related structures, it was possible to predict qualitatively their modulating activity. Enterodiol (25 mg L-1) reduced the bitterness of the 500 mg L-1 caffeine solution by about 30%, whereas enterolactone showed no masking but a slight bitter-enhancing effect.
- Ley, Jakob P.,Dessoy, Marco,Paetz, Susanne,Blings, Maria,Hoffmann-Lücke, Petra,Reichelt, Katharina V.,Krammer, Gerhard E.,Pienkny, Silke,Brandt, Wolfgang,Wessjohann, Ludger
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- A Direct Synthesis of 2-(ω-Carboxyalkyl)isoflavones from ortho-Hydroxylated Deoxybenzoins
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As part of a program focused on the development of new antineoplastic agents based on scaffolds found in natural products, we explored the isoflavone family as potential enzyme inhibitors. We required biotin-modified isoflavones to identify potential biological targets, and we selected the C-2 position in isoflavones as an attachment site for an alkyl group bearing a terminal carboxylic acid to which we could attach a biotin derivative. The base-catalyzed condensation of 2,4-dihydroxy-substituted deoxybenzoins with cyclic anhydrides mediated by a combination of triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene led to an efficient synthesis of the desired 2-(ω-carboxyalkyl)isoflavones with functional groups at C-5, 6 and 7 and with various substituents in the C-3 phenyl group.
- Mrug, Galyna P.,Demydchuk, Bohdan A.,Bondarenko, Svitlana P.,Sviripa, Vitaliy M.,Wyrebek, Przemyslaw,Mohler, James L.,Fiandalo, Michael V.,Liu, Chunming,Frasinyuk, Mykhaylo S.,Watt, David S.
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supporting information
p. 5460 - 5463
(2018/10/20)
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- Technical Process for Preparation of Genistein
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Development and scale-up of the synthetic process for genistein preparation are described. The process was designed with consideration for environmental and economical aspects and optimized in a laboratory scale. In a scale up, on every step quantity of the environmentally unfriendly substrates or solvents was reduced without compromising the quality of the final product, and the waste load was significantly diminished. The optimal duration times of the individual stages were determined, and the number of operations was reduced, leading to lowering of energy consumption. Elaborated process secures good yield and quality expected for pharmaceutical substances.
- Filip, Katarzyna,Kleczkowska-Plichta, Ewa,Ara?ny, Zbigniew,Grynkiewicz, Grzegorz,Polowczyk, Magdalena,Gabarski, Krzysztof,Trzcińska, Kinga
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p. 1354 - 1362
(2016/07/23)
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- Multifunctional deoxybenzoin-based monomers and resins having reduced flammability
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The invention provides a novel platform for minimal- or non-flammable polymers, which is based purely on hydrocarbon systems and does not need additives of any kind A key feature is that the hydrocarbons disclosed herein are characterized by degradation mechanisms that produce few flammable volatiles. For example, 2,4,4′,6-tetrahydroxydeoxybenzoin is employed as a multifunctional cross-linker in conjunction with bis-epoxydeoxybenzoin, affording new resins that combine excellent physical and mechanical properties with low flammability.
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Page/Page column 10
(2016/08/10)
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- Multifunctional deoxybenzoin-based epoxies: Synthesis, mechanical properties, and thermal evaluation
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We describe 2,4,4′,6-tetrahydroxydeoxybenzoin (THDB) as a multifunctional cross-linker in conjunction with bis-epoxydeoxybenzoin (BEDB), affording new resins that combine excellent physical and mechanical properties with low flammability. The char residue and heat release capacity values of the cross-linked epoxies were measured by thermogravimetric analysis (TGA) and pyrolysis combustion flow calorimetry (PCFC), respectively. Resins fabricated from THDB exhibited low total heat release (13 kJ/g) and high char yields (34%), as well as good mechanical properties, making them suitable candidates for consideration in high performance adhesive applications. The desirable heat release and char yield properties of these structures are realized without the presence of any conventional flame retardant, such as halogenated structures or inorganic fillers that are commonly utilized in commercial materials.
- Szyndler, Megan W.,Timmons, Justin C.,Yang, Zhan H.,Lesser, Alan J.,Emrick, Todd
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p. 4441 - 4446
(2014/10/15)
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- Arylalkyl ketones, benzophenones, desoxybenzoins and chalcones inhibit TNF-α induced expression of ICAM-1: Structure-activity analysis
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The interaction between leukocytes and the vascular endothelial cells (EC) via cellular adhesion molecules plays an important role in the pathogenesis of various inflammatory and autoimmune diseases. Small molecules that block these interactions have been targeted as potential therapeutic agents against acute and chronic inflammatory diseases. In an effort to identify potent intercellular cell adhesion molecule-1 (ICAM-1) inhibitors, a large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones and their analogs (54 in total) have been synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated the possible mechanism for their ICAM-1 inhibitory activities. The most active compound was found to be 79. A large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones as well as their analogs (54 in total) were synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated a possible mechanism of their ICAM-1 inhibitory activities. The most active compound was found to be 79. Copyright
- Kumar, Sarvesh,Reddy L, Chandra Shekhar,Kumar, Yogesh,Kumar, Amit,Singh, Brajendra K.,Kumar, Vineet,Malhotra, Shashwat,Pandey, Mukesh K.,Jain, Rajni,Thimmulappa, Rajesh,Sharma, Sunil K.,Prasad, Ashok K.,Biswal, Shyam,Van Der Eycken, Erik,Depass, Anthony L.,Malhotra, Sanjay V.,Ghosh, Balaram,Parmar, Virinder S.
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experimental part
p. 368 - 377
(2012/07/31)
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- Synthesis of Talosin A and B, two bioactive isoflavonoid glycosides
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Talosin A and B, namely genistein 7-O-α-L-6-deoxy-talopyranoside and genistein 4',7-di-O-α-L-6-deoxytalopyranoside, which show excellent antifungal and anti-inflammatory activities, were synthesized concisely.
- Wu, Zhongtao,Lian, Gaoyana,Yu, Biao,Wang, Zhenzhongc,Zhao, Yiwuc,Xiao, Wei
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scheme or table
p. 1725 - 1730
(2011/07/07)
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- Synthesis and structure-activity relationship study of deoxybenzoins on relaxing effects of porcine coronary artery
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Deoxybenzoins are potent antioxidants and tyrosinase inhibitors with potential to be developed as food preservatives and cosmetic ingredients. To explore the potential in cardiovascular protection, 25 polyphenolic deoxybenzoins were synthesized and evaluated for inhibitory effects on KCl-induced porcine coronary arterial contraction. The results revealed deoxybenzoins are significant inhibitors of KCl-induced arterial contraction. Among those synthesized, two-thirds of the deoxybenzoins exhibited moderate to good efficacy on relaxing contracted artery including 2,4-dihydroxydeoxybenzoin with EC50 = 3.30 μM (Emax = 100%, n = 7) and 2,4-dihydroxy-4′-methoxydeoxybenzoin EC50 = 3.70 μM (E max = 100%, n = 5). Deoxybenzoins displayed an endothelium-dependent relaxing manner on the contracted artery; the contractile responses of neither endothelium denuded nor L-NAME deactivated rings were inhibited. The structure-activity relationships of deoxybenzoin on arterial relaxing effects concluded that the 2,4-dihydroxylated deoxybenzoins presented a potential vascular relaxing pharmacophore, with favoring substitution on ring B in the order of H ≤ p-OMe > p-OH > o-OMe > m,p-diOMe ≤ m-OMe.
- Lu, Tzy-Ming,Kuo, Daih-Huang,Ko, Horng-Huey,Ng, Lean-Teik
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experimental part
p. 10027 - 10032
(2011/05/17)
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- 7-Hydroxy-benzopyran-4-one derivatives: A novel pharmacophore of peroxisome proliferator-activated receptor α and -γ (PPARα and γ) dual agonists
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Design, synthesis, and in vitro bioevaluation of a new class of potential dual PPARα and γ agonists discovered through a structure-driven design paradigm are described. The 7-hydroxy-benzopyran-4-one moiety (includes flavones, flavanones, and isoflavones) is the key pharmacophore of these novel molecules, exhibiting similarity to the core structure of both fibrates and thiazolidinediones. New lead PPAR ligands were identified from "natraceuticals" and synthetic analogues. In total, 77 molecules, including chalcones, flavones, flavanones, isoflavones, and pyrazole derivatives, were screened and structure-activity relationship studies of the dual agonists undertaken. Compounds 68, 70, 72, and 76 were identified as novel and potent dual PPARα and γ agonists. These novel molecules may have the potential to be the future leads in PPAR-related disorders, including type II diabetes mellitus and metabolic syndrome. 2009 American Chemical Society.
- Matin, Azadeh,Gavande, Navnath,Kim, Moon S.,Yang, Nancy X.,Salam, Noeris K.,Hanrahan, Jane R.,Roubin, Rebecca H.,Hibbs, David E.
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experimental part
p. 6835 - 6850
(2010/04/04)
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- Potential antioxidants and tyrosinase inhibitors from synthetic polyphenolic deoxybenzoins
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Deoxybenzoins (DOBs) are one-pot synthetic precursors of isoflavones with feature analogous to those beneficial polyphenols such as resveratrol (stilbene) and phloretin (dihydrochalcone). In this study, seventeen polyphenolic DOBs were synthesized and evaluated by various antioxidant assays and tyrosinase inhibitory effect in vitro. Results displayed that these DOBs are powerful antioxidants; for example, 2,3,4-trihydroxy-3′,4′-dimethoxydeoxybenzoin possesses an excellent anti-lipid peroxidation activity (IC50 = 0.72 ± 0.16 μM), whilst 2,4,4′,5-tetrahydroxydeoxybenzoin showed good DPPH radical scavenging activity (IC50 = 0.69 ± 0.04 μM), which were better than Trolox and vitamin C. Besides exhibiting a weak metal chelating effect, these DOBs were effective in scavenging ABTS{radical dot}+ and superoxide anion (O2{radical dot} -) radicals. DOBs also exhibited potent mushroom tyrosinase inhibitory activity; for example 2,3,4′-trihydroxy-4-methoxydeoxybenzoin displayed stable and significant inhibitory effect on tyrosinase activity, with IC50 values 43.37, 43.10 and 46.10 μM at incubation intervals of 0.5, 1.5, and 2.5 h, respectively. These results suggest that, with the advantage of being readily synthesizable small molecules, DOBs can be potentially developed into clinical and industrial antioxidants. Crown Copyright
- Ng, Lean-Teik,Ko, Horng-Huey,Lu, Tzy-Ming
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experimental part
p. 4360 - 4366
(2009/10/17)
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- Synthesis, crystal structure and antimicrobial activity of deoxybenzoin derivatives from genistein
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A series of deoxybenzoin derivatives from genistein were synthesized and their structures were elucidated by 1H NMR, mass spectral data and micro analyses. The structures of 2, 7 and 10 were determined by single-crystal X-ray analysis. These obtained compounds were evaluated for their assayed antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescence and Staphylococcus aureus) and antifungal (Aspergillus niger, Candida albicans and Trichophyton rubrum) activities by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) method. Most compounds have displayed comparable antibacterial activity against bacterial. On the basis of the biological results, structure-activity relationships are discussed.
- Li, Huan-Qiu,Xue, Jia-Yu,Shi, Lei,Gui, Shan-Ying,Zhu, Hai-Liang
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p. 662 - 667
(2008/09/20)
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- Polyphenols based on isoflavones as inhibitors of Helicobacter pylori urease
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Twenty polyphenols were synthesized and evaluated for their effect on Helicobacter pylori urease. Among these compounds, 4-(p-hydroxyphenethyl)pyrogallol (15) (IC50 = 0.03 mM) and 7,8,4′-trihydroxyisoflavone (19) (IC50 = 0.14 mM) showed potent inhibitory activities, and inhibited Helicobacter pylori urease in a time-dependent manner. The structure-activity relationship of these polyphenols revealed: the two ortho hydroxyl groups were essential for inhibitory activity of polyphenol. When the C-ring of isoflavone was broken, the inhibitory activity markedly decreased. As for deoxybenzoin, the carboxyl group was clearly detrimental.
- Xiao, Zhu-Ping,Shi, Da-Hua,Li, Huan-Qiu,Zhang, Li-Na,Xu, Chen,Zhu, Hai-Liang
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p. 3703 - 3710
(2008/02/07)
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- PROCESS FOR THE MANUFACTURE OF HYDROXYLATED ISOFLAVONES
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A process for the preparation of hydroxylated isoflavones by reacting in a Hoesch reaction using an alkanoic acid alkyl ester as solvent a phenol with a phenylacetonitrile to yield a 1,2-diphenyl-ethanone and transforming the ethanone into an isoflavone by well-known methods.
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Page/Page column 7
(2008/06/13)
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- Estrogens for treating ALS
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A method for preventing and treating ALS by administering a phytoestrogen, preferably genistein.
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(2008/06/13)
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- The first isolation and crystal structure of a boron difluoro complex (isoflavone yellow). Biologically active intermediates produced during isoflavone synthesis
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The yellow intermediate 4f produced during the reaction of the deoxybenzoin 3f with N,N'-dimethyl(chloromethylene)ammonium chloride in the presence of BF3*Et2O prior to the formation of the corresponding isoflavone was isolated for the first time and characterized by NMR, MS and single-crystal X-ray diffraction techniques. These yellow intermediates showed anticancer, nematicidal and mosquitocidal activities.
- Balasubramanian, Sreenivasan,Ward, Donald L.,Nair, Muraleedharan G.
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p. 567 - 570
(2007/10/03)
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- Expedient Synthesis of Polyhydroxyisoflavones
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A general and direct synthesis of polyhydroxy isoflavones (3-phenyl-4H-1-benzopyran-4-ones) starting from the corresponding unprotected phenols and arylacetic acids is described.The aryl rings may carry additional alkyl, methoxy and/or halogeno groups.Intermediate polyhydroxydeoxybenzoins (1,2-diphenylethanones) can also be isolated in good yields.
- Waehaelae, Kristiina,Hase, Tapio A.
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p. 3005 - 3008
(2007/10/02)
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